Most of the time, you need not tip more than 20 percent, but here are some occasions when you should be more generous:
1. Exceptional service where you wouldn’t expect it. If the waiter arranges a special pasta dish for you, sings happy birthday to your daughter, or replenishes that drink you just finished off without asking. But only if the service goes way beyond what you’d expect for the type of restaurant it is.
2. Freebies. If the server brings out complimentary chocolate cake, then you should tip on the estimated cost of the comped items. These might include waived corkage, which will ultimately mean larger tip.
3. Getting treated like a regular. Being treated as family at a restaurant you visit on a regular basis always calls for a larger tip. When someone calls you “my darling,” gives you a sense of loving nature and part of a family.
4. A small check. Sometimes the check is so low that 20 percent seems absurd. If that ends up being the case, just leave a couple of dollars or so.
5. A “camping” aka “lingering” tip. If you linger (known as “camping” in restaurant lingo), you should definitely compensate the server for the lost business. Even if the place is empty, you should augment your tip a bit, because the waiter may have offered you more service such as re-filling your water glass or asking if you want anything else.
6. A pity tip. If the server looks like a lost malnourished college student who is living on ramen noodles, or a stressed out staff member running around like a chicken with his head cut off.
